Cruel Intentions
by darolinesalvatore
Summary: Elena Gilbert unwittingly becomes a pawn in Damon Salvatore's and Katherine Pierce's deliciously diabolical wager of sexual conquest when she's the new girl in Mystic Falls, she's a virgin, and intends to stay that way until she marries her boyfriend. However, Damon gets more than he bargained for as he attempts to get Elena into his bed.
1. Chapter 1

**CRUEL INTENTIONS**

 _ **Chapter One**_

It was a beautiful morning in Mystic Falls, the sky was overcast in dark clouds, but the air was warm and children were playing all around. Inside, Mikaelson Estate an elder women, sat at her desk scribbling down notes and frowning as the young man in front of her fidgets with a pen looking impatient.

"We've been at this for six months Damon." Ester Mikaelson said as she throws her glasses on to the table tiredly.

"I know." Damon replied, rolling his eyes. He pulls out a small flask from inside his black leather jacket. Ester stands up and grabs the flask from his hands, giving him a glare.

"There is no drinking in my office." She throws the flask into the rubbish bin next to her desk, Damon sneers at the women as she sits back down.

"What do you want me to say doc? That I feel remorse because I act the way I do?" He smirks, "Because I don't. Not one bit." Ester shakes her head and continues to scribble down notes, Damon clearly annoyed stands up and walks around her office. "I get it, I'm not like my goody two shoes brother, you're all so _dissapointed_ in me, truth is, I don't really care," He shrugs his shoulders, "I don't care about report cards or extra credit. The only challenge that I see are women." Ester rolls her eyes while Damon continues, "You see a girl you like, you pursue her, you conquer and then you move on, it's exciting."

"That's all you care about?" Ester narrowed her eyes, "You have the worst reputation, don't you want to change that? Be better?"

Damon chuckles shaking his head staring at the doctor, "Women love a man with a bad reputation, they all think they're going to _save me?_ I just let them think they will, that's the trick... oh, and of course my unflinching ability to listen to Taylor Swift."

Ester, clearly baffled throws her notepad onto her desk, "That's all for today Damon."

"Oh, but we were just getting somewhere." Damon replied sarcastically, "same time next week?"

"No... this will be our last session, I will have to tell your parents you aren't taking this seriously." Ester shook her head, "Your parents spend a lot of money for these sessions. I'm only trying to help you."

"Oh you do help me Doc, I'm already feeling my path to redemption coming towards me." Damon smirked.

"I hope you grow up one day Damon, otherwise you're going to get in trouble." Damon walks towards Ester's desk approaching a photograph of her young daughter Rebekah. Ester watched Damon while scribbling notes down, "that's my daughter Rebekah."

"She looks... _delicious."_ Damon whistles, licking his lips.

Ester rolls her eyes, "she would never go for a man with your morals, she is attending Whitmore this fall. She is way too smart to fall for your charm." Ester humped, grabbing the photograph out of Damon's hands.

Damon raised a brow, "Care to make a bet?"

"Goodbye Damon, I hope you get the help you need. You clearly need it." Ester opened the door while Damon puts on his sunglasses, he leans down towards the rubbish bin and grabs his flask. He walks out with a strut and Ester shuts the door behind him, "thank goodness for that" she mumbles. Ester walks back around to her desk waiting for her next session as her daughter rings. "Hello love, how are you?"

 _"Mum?"_

"Rebekah, what's wrong?" She could hear her daughter crying over the phone.

 _"He told me he loved me... I'm so stupid."_

"Who told you?"

 _"You won't know him... there's pictures of me on the internet mum!"_

Ester sighs putting her face into her hands, "Rebekah, how could you be so stupid!"

 _"He was so charming, he kept telling me that I could be the one to change him if I just opened up to him... things just got out of hand."_ Rebekah cried. She could hear the drop of the phone from the other line. _"Mum?"_

Ester Mikaelson ran through the halls looking for her target. Damon Salvatore. She spots him standing inside of an elevator speaking to a young women, "You son of a bitch!" She screamed racing for him, the doors shut which caused her to scream in rage and bang on the elevator doors abruptly.

Damon smirks as he walks out of the building and towards his camero. "Another one down..." He whispers, deleting Rebekah Mikaelson's number from his phone.


	2. Chapter 2

_**C**_ **ruel Intentions**

 _ **Chapter Two**_

Katherine Pierce sits in the parlor room of the Boarding House, how she had wished she wasn't there and somewhere else would have been slumming it. Katherine watches the two females in front of her, one in her mid forties and the other just a cute and innocent sixteen year old girl who didn't know what was in store for her; she smiled to herself, not because of Mrs Forbes pathetic attempt at a joke, but because she was going to ruin her sickly sweet darling daughter Caroline.

"I am very happy that Caroline is attending Mystic Falls High with you this year Katherine, you've always been an inspiration to both Bill and I in raising her." Elizabeth Forbes glanced at her daughter giving her a curt smile, "we just hope she can rise to your expectations for her."

Katherine mimicked Mrs Forbes smile, "I'll do my best." In her head, she was doing the complete opposite. How she hated the Forbes, most of them were all in the Police Department and were one of the Founding Families in Mystic Falls, which meant Katherine had to be exceptionally nice to them.

"Katherine is a straight-A student as well as being President of the French Club." Liz proudly states, Caroline however, looked bored as she twaddled her thumbs. "Listen to whatever she says and you'll go far Caroline."

"Oh, you're too kind Mrs Forbes."

"How do you do it?" Liz sighs, "with all the peer pressuring and drugs and alcohol that go around, where do you get your strength?"

Katherine smiled feeling her crucifix around her neck, "as corny as this sounds, whenever I feel a temptation or a need I turn to god and he helps me." Little did they know, what was inside that crucifix.

"That is something..." Liz admires.

"Is there cheer-leading?" Caroline sits up suddenly, it took all her might for Katherine to not roll her eyes, she hated that little bitch. "I was head captain at my old school."Caroline states proudly.

Katherine growled under her breath, _of course you were you preppy bitch._ "Yes, there is a cheer-leading squad, they cheer for the football team."

"What about the boys?' Caroline winked at Katherine, Katherine chuckled. "What are they like?"

"Caroline!" Liz squealed, "is that all you can think about?" Liz grabbed Katherine's hands, "please forgive her, she's a little over excited from the drive over here."

"Don't worry about it." Katherine smiled, "the boys at Mystic Falls High are respectable young men, Stefan Salvatore one of them, he's the Team Captain of the Wolverines, but at every school you're going to have a few bad apples." Katherine shrugged.

"Like your step brother Damon." Liz darkened, "that one is a bad apple, in a family of well respected, like yourself and Stefan, I wonder what Damon missed." She shook her head, "I still can't believe he got kicked out of school, I couldn't imagine what his father would say."

"Actually he took it quite well." Damon smirked as he walked into the parlor room where the three were sitting. Liz sneers at Damon while Caroline drawls, Katherine smirked, this would be easy. Damon took a seat right across from the two Forbes as Katherine turned to her step-brother. "Good to see you again Caroline, how long has it been?"

"A few years." Caroline replied, blushing.

"Haven't you grown into a..." Damon took in the young girl, from her blonde locks to her young supple breasts, she had grown up. If any other case, he would sleep with her, not for amusement but because she was stunning, but it would've been too easy, "beautiful women." He smirked, finishing his sentence. He could feel Liz Forbes eyes pinning him to the ground.

"Caroline is attending Mystic High this year." Liz said, gritting her teeth.

"Which means we're going to see each other a lot more now." Damon winked.

Caroline smiled, tucking her hair behind her ear, "didn't you get kicked out?"

Damon shrugged, "they'll let me back in, my father practically owns this town, they'd be stupid not too." He sighed, "plus my little brother is royalty there and no one would want the Salvatore Brothers to be broken."

"I think we should be going." Liz takes Caroline's arms in hers as they stand up. She turns to Katherine, "thanks for all your help Katherine, we'll see ourselves out."

"We'll talk more about everything later." Katherine grins taking Caroline hands. The two Forbes walked out, as soon as that happened, the sweet smile on Katherine's olive face darkened. She turned back around to Damon who was smirking as he poured himself a glass of bourbon. Katherine sultry stepped towards him as he handed her a glass.

"Care to tell me why Legally Blonde was in my house?" Damon asked.

Katherine smirked, "I'm just taking the poor girl under my wing." She sits down on the leather sofa next to Damon, she takes her crucifix out unscrewing the lid revealing a white substance. "The parental units called while you were out."

Damon raised a brow watching Katherine, "Well, how is your gold digging whore of a mother enjoying Italy? Zipping through my fathers money as per usual."

Katherine humps, "She suspects your father is having an affair." Damon rolls his eyes standing up, "what is wrong with you today? Therapy not go well?" She chuckles.

"It was fine." Damon shrugs, "I'm just sick of sleeping with these small town high school girls. Nothing shocks me anymore." He sighs. "I'm bored basically."

"Well you can relax, I have a mission for you." Katherine smirked.


End file.
